A New Synthetic Method of Peptide-Chitosan Conjugates:Solid-Phase Synthesis of GHK Coupled to Chitosan

Byung-Jo Ha; Ok-Sub Lee; Yoon-Sik Lee

Journal of Industrial and Engineering Chemistry, Vol.1, No.1, 57-63, December, 1995

Byung-Jo Ha, Ok-Sub Lee, and Yoon-Sik Lee¹

Pacific R & D Center, Bora-Ri, Kiheung-Up, Yongin-Kun, Kyunggi-Do 449-900, Korea
¹Dept. of Chem. Technology, College of Eng., Seoul National Univ., Seoul 151-742, Korea

A novel method was developed for the solid-phase synthesis of Glycyl-L-histidyl-L-lysine(GHK)-chitosan conjugates, using a Fmoc-amino acids/BOP coupling reaction. For this purpose, the beads which had a mean diameter of 70μm were prepared by the W/O emulsion-phase separation method. The characteristics of the beads as a solid support have also been investigated. The physical properties of this new solid support were quite different from those of the classical polystyrene-based beads. The new support had high swelling ability in water and higher amine content tahn commercial solid supports for peptide synthesis. Model tripeptide, GHK, was successfully coupled to the chitosan beads. They were fluorescence labeled to examine the release pattern of the GHK-chitosan conjugates by lysozyme.

[References]

Gudmund SB, Thorleif A, Paul S, "Chitin and Chitosan," Elsevier Science Publishers, New York (1989)
Miyazaki S, Ishii K, Nadai T, Chem. Pharm. Bull., 29, 3067 (1981)
Kost J, Langer R, Trends Biotechnol., 10, 127 (1992)
Ouchi T, Banba T, Fujimoto M, hamamoto S, Makromol. Chem., 190, 1817 (1989)
Hirano S, Kondo S, Ohe Y, Polymer, 16, 622 (1975)
Al-Shamkhani A, Duncan R, J. Bioactive Compat. Polym., 10, 4 (1995)
Gurruchaga M, Goffi I, Valero M, Guzman GM, Polymer, 33, 3274 (1992)
Kim JH, Kim JY, Lee YM, Kim KY, J. Appl. Polym. Sci., 44, 1823 (1992)
Nakamura F, Onishi H, Machida Y, Nagai T, Yakuzaigaku, 52, 59 (1992)
Pickart L, Lovejoy S, "Methods in Enzymology," D. Barues, D.A. Sirbasku, Eds. Vol. 147, Academic Press, New York, p. 314 (1987)
Pickart L, Lymphokines, 8, 425 (1983)
Perin DD, Armarego WLF, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford (1988)
Mima S, Miya M, Iwamoto R, Yosikawa S, J. Appl. Polym. Sci., 28, 1909 (1983)
Sakai K, Uchiyama T, Matahira Y, Nanjo F, J. Ferment. Bioeng., 72, 168 (1991)
Stewart JM, Young JD, "Solid Phase Peptide Synthesis," Pierce Chemical Company, Rockford IL, p. 125 (1984)
Neugebauer WA, Carbohydr. Res., 189, 363 (1989)
Gisin BF, Anal. Chim. Acta, 58, 248 (1972)
Grant GA, "Synthetic Peptides: A User's Guide," W.H. Freeman and Company, New York, p. 119 (1992)
Kaiser ET, Colescott RL, Cook PI, Anal. Biochem., 34, 595 (1970)

[Referenced By]

[Related Articles]

[1] Gudmund SB, Thorleif A, Paul S, "Chitin and Chitosan," Elsevier Science Publishers, New York (1989)

[2] Miyazaki S, Ishii K, Nadai T, Chem. Pharm. Bull., 29, 3067 (1981)

[3] Kost J, Langer R, Trends Biotechnol., 10, 127 (1992)

[4] Ouchi T, Banba T, Fujimoto M, hamamoto S, Makromol. Chem., 190, 1817 (1989)

[5] Hirano S, Kondo S, Ohe Y, Polymer, 16, 622 (1975)

[6] Al-Shamkhani A, Duncan R, J. Bioactive Compat. Polym., 10, 4 (1995)

[7] Gurruchaga M, Goffi I, Valero M, Guzman GM, Polymer, 33, 3274 (1992)

[8] Kim JH, Kim JY, Lee YM, Kim KY, J. Appl. Polym. Sci., 44, 1823 (1992)

[9] Nakamura F, Onishi H, Machida Y, Nagai T, Yakuzaigaku, 52, 59 (1992)

[10] Pickart L, Lovejoy S, "Methods in Enzymology," D. Barues, D.A. Sirbasku, Eds. Vol. 147, Academic Press, New York, p. 314 (1987)

[11] Pickart L, Lymphokines, 8, 425 (1983)

[12] Perin DD, Armarego WLF, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford (1988)

[13] Mima S, Miya M, Iwamoto R, Yosikawa S, J. Appl. Polym. Sci., 28, 1909 (1983)

[14] Sakai K, Uchiyama T, Matahira Y, Nanjo F, J. Ferment. Bioeng., 72, 168 (1991)

[15] Stewart JM, Young JD, "Solid Phase Peptide Synthesis," Pierce Chemical Company, Rockford IL, p. 125 (1984)

[16] Neugebauer WA, Carbohydr. Res., 189, 363 (1989)

[17] Gisin BF, Anal. Chim. Acta, 58, 248 (1972)

[18] Grant GA, "Synthetic Peptides: A User's Guide," W.H. Freeman and Company, New York, p. 119 (1992)

[19] Kaiser ET, Colescott RL, Cook PI, Anal. Biochem., 34, 595 (1970)